Artem Kireev - Synthesis and Biological Evaluation of Aromatic Analogs of Conduritol F, L-chiro-Inositol and Dihydroconduritol F Structurally Related to the Amaryllidaceae Anticancer Constituents

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  Publication Details (including relevant citation   information):

  J. Org. Chem. 2006, 71, 5694


  Pancratistatin is a potent anticancer natural product, whose   clinical  evaluation is hampered by the limited natural   abundance and the  stereochemically complex structure   undermining practical chemical  preparation. Fifteen   aromatic analogues of conduritol F,   l-chiro-inositol,  and dihydroconduritol F that   possess four of the six pancratistatin  stereocenters have   been synthesized and evaluated for anticancer  activity.   These compounds serve as truncated pancratistatin analogues    lacking the lactam ring B, but retaining the crucial C10a−C10b   bond with  the correct stereochemistry. The lack of activity   of these compounds  provides further insight into   pancratistatin's minimum structural  requirements for   cytotoxicity, particularly the criticality of the  intact   phenanthridone skeleton. Significantly, these series provide   rare  examples of simple aromatic conduritol and inositol   analogues and,  therefore, this study expands the chemistry   and biology of these  important classes of compounds.

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